TWI291956B - Improved process - Google Patents
Improved process Download PDFInfo
- Publication number
- TWI291956B TWI291956B TW093121917A TW93121917A TWI291956B TW I291956 B TWI291956 B TW I291956B TW 093121917 A TW093121917 A TW 093121917A TW 93121917 A TW93121917 A TW 93121917A TW I291956 B TWI291956 B TW I291956B
- Authority
- TW
- Taiwan
- Prior art keywords
- solution
- eletriptan
- water
- acid
- mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 14
- 229960002472 eletriptan Drugs 0.000 claims description 14
- OTLDLQZJRFYOJR-LJQANCHMSA-N eletriptan Chemical compound CN1CCC[C@@H]1CC1=CN=C2[C]1C=C(CCS(=O)(=O)C=1C=CC=CC=1)C=C2 OTLDLQZJRFYOJR-LJQANCHMSA-N 0.000 claims description 14
- 229960003470 eletriptan hydrobromide Drugs 0.000 claims description 14
- UTINOWOSWSPFLJ-FSRHSHDFSA-N eletriptan hydrobromide Chemical compound Br.CN1CCC[C@@H]1CC(C1=C2)=CNC1=CC=C2CCS(=O)(=O)C1=CC=CC=C1 UTINOWOSWSPFLJ-FSRHSHDFSA-N 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- -1 indolylpyrrolidine-2-ylmethyl Chemical group 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 2
- UJTPZISIAWDGFF-UHFFFAOYSA-N ethenylsulfonylbenzene Chemical group C=CS(=O)(=O)C1=CC=CC=C1 UJTPZISIAWDGFF-UHFFFAOYSA-N 0.000 claims description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 1
- 230000000887 hydrating effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 229910052747 lanthanoid Inorganic materials 0.000 claims 1
- 150000002602 lanthanoids Chemical class 0.000 claims 1
- 239000002324 mouth wash Substances 0.000 claims 1
- 229940051866 mouthwash Drugs 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 239000000047 product Substances 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 16
- 238000001914 filtration Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000012066 reaction slurry Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- VZXXYILNWWRSGE-UHFFFAOYSA-N 3,5-dimethylheptan-4-one Chemical compound CCC(C)C(=O)C(C)CC VZXXYILNWWRSGE-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 241000239226 Scorpiones Species 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- QNEFNFIKZWUAEQ-UHFFFAOYSA-N carbonic acid;potassium Chemical compound [K].OC(O)=O QNEFNFIKZWUAEQ-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0317229.3A GB0317229D0 (en) | 2003-07-23 | 2003-07-23 | Improved process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200510388A TW200510388A (en) | 2005-03-16 |
| TWI291956B true TWI291956B (en) | 2008-01-01 |
Family
ID=27772518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW093121917A TWI291956B (en) | 2003-07-23 | 2004-07-22 | Improved process |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP1660485B1 (es) |
| JP (1) | JP2006528172A (es) |
| KR (1) | KR100694962B1 (es) |
| CN (1) | CN100430388C (es) |
| AR (1) | AR046509A1 (es) |
| AT (1) | ATE349442T1 (es) |
| AU (1) | AU2004256994A1 (es) |
| BR (1) | BRPI0412721A (es) |
| CA (1) | CA2532111A1 (es) |
| CO (1) | CO5650232A2 (es) |
| CY (1) | CY1105980T1 (es) |
| DE (1) | DE602004003966T2 (es) |
| DK (1) | DK1660485T3 (es) |
| ES (1) | ES2274473T3 (es) |
| GB (1) | GB0317229D0 (es) |
| IL (1) | IL172765A0 (es) |
| MX (1) | MXPA06000793A (es) |
| NO (1) | NO20056238L (es) |
| NZ (1) | NZ544305A (es) |
| PL (1) | PL1660485T3 (es) |
| PT (1) | PT1660485E (es) |
| RU (1) | RU2320655C2 (es) |
| TW (1) | TWI291956B (es) |
| WO (1) | WO2005007649A1 (es) |
| ZA (1) | ZA200600607B (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101139557B1 (ko) | 2003-07-23 | 2012-04-30 | 바이엘 파마슈티칼스 코포레이션 | 질환 및 상태의 치료 및 예방을 위한 플루오로 치환오메가-카르복시아릴 디페닐 우레아 |
| JP5214124B2 (ja) | 2006-08-17 | 2013-06-19 | 三星電子株式会社 | 通信システム、通信装置、尤度計算方法、及びプログラム |
| US20090299077A1 (en) * | 2008-05-22 | 2009-12-03 | Vinod Kumar Kansal | Salts of (R)-5-(2phenylsulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole, 5-bromo-3-[(R)-1-methyl-pyrrolidin-2-ylmethyl]-1H-indole and of eletriptan |
| WO2010116386A2 (en) * | 2009-04-08 | 2010-10-14 | Biophore India Pharmaceuticals Pvt. Ltd. | Novel polymorph of eletriptan hydrobromide and process for the preparation thereof |
| IT1393700B1 (it) * | 2009-04-22 | 2012-05-08 | F S I Fabbrica Italiana Sint | Sintesi di 3-{[(2r)-1-metilpirrolidin-2-il]metil}-5-[2-(fenilsulfonil)etil]-1h-indolo |
| WO2011004391A2 (en) * | 2009-06-25 | 2011-01-13 | Matrix Laboratories Ltd | An improved process for the preparation of eletriptan and its salt thereof |
| WO2011089614A1 (en) * | 2010-01-19 | 2011-07-28 | Sms Pharmaceuticals Limited | PROCESS FOR PREPARING ELETRIPTAN HYDROBROMIDE HAVING α-FORM |
| WO2012004811A1 (en) * | 2010-07-06 | 2012-01-12 | Ind-Swift Laboratories Limited | Process for the preparation of 5-substsituted indole derivative |
| CN102786514B (zh) * | 2012-07-26 | 2014-01-29 | 武汉人福医药集团股份有限公司 | 依来曲普坦的制备方法 |
| CN104341397A (zh) * | 2013-07-31 | 2015-02-11 | 上海威智医药科技有限公司 | 具晶型的依来曲普坦自由碱及其制法和应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW288010B (es) * | 1992-03-05 | 1996-10-11 | Pfizer | |
| FR2701026B1 (fr) * | 1993-02-02 | 1995-03-31 | Adir | Nouveaux dérivés de l'indole, de l'indazole et du benzisoxazole, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
| AU3217295A (en) * | 1994-08-12 | 1996-03-07 | Donald D. II Thomas | Miniaturized blood pressure monitor kit |
| GB9417310D0 (en) * | 1994-08-27 | 1994-10-19 | Pfizer Ltd | Therapeutic agents |
| GB9825988D0 (en) * | 1998-11-27 | 1999-01-20 | Pfizer Ltd | Indole derivatives |
| GB0031094D0 (en) * | 2000-12-20 | 2001-01-31 | Pfizer Ltd | New Process |
-
2003
- 2003-07-23 GB GBGB0317229.3A patent/GB0317229D0/en not_active Ceased
-
2004
- 2004-07-12 CA CA002532111A patent/CA2532111A1/en not_active Abandoned
- 2004-07-12 DE DE602004003966T patent/DE602004003966T2/de not_active Expired - Fee Related
- 2004-07-12 AU AU2004256994A patent/AU2004256994A1/en not_active Abandoned
- 2004-07-12 DK DK04743983T patent/DK1660485T3/da active
- 2004-07-12 BR BRPI0412721-8A patent/BRPI0412721A/pt not_active IP Right Cessation
- 2004-07-12 NZ NZ544305A patent/NZ544305A/en unknown
- 2004-07-12 MX MXPA06000793A patent/MXPA06000793A/es active IP Right Grant
- 2004-07-12 EP EP04743983A patent/EP1660485B1/en not_active Expired - Lifetime
- 2004-07-12 RU RU2006101689/04A patent/RU2320655C2/ru not_active IP Right Cessation
- 2004-07-12 KR KR1020067001359A patent/KR100694962B1/ko not_active Expired - Fee Related
- 2004-07-12 PL PL04743983T patent/PL1660485T3/pl unknown
- 2004-07-12 JP JP2006520921A patent/JP2006528172A/ja not_active Withdrawn
- 2004-07-12 AT AT04743983T patent/ATE349442T1/de not_active IP Right Cessation
- 2004-07-12 WO PCT/IB2004/002322 patent/WO2005007649A1/en not_active Ceased
- 2004-07-12 CN CNB2004800204126A patent/CN100430388C/zh not_active Expired - Fee Related
- 2004-07-12 PT PT04743983T patent/PT1660485E/pt unknown
- 2004-07-12 ES ES04743983T patent/ES2274473T3/es not_active Expired - Lifetime
- 2004-07-21 AR ARP040102584A patent/AR046509A1/es unknown
- 2004-07-22 TW TW093121917A patent/TWI291956B/zh active
-
2005
- 2005-12-22 IL IL172765A patent/IL172765A0/en unknown
- 2005-12-27 CO CO05130436A patent/CO5650232A2/es not_active Application Discontinuation
- 2005-12-30 NO NO20056238A patent/NO20056238L/no not_active Application Discontinuation
-
2006
- 2006-01-20 ZA ZA200600607A patent/ZA200600607B/en unknown
-
2007
- 2007-02-01 CY CY20071100145T patent/CY1105980T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ544305A (en) | 2008-09-26 |
| RU2320655C2 (ru) | 2008-03-27 |
| AR046509A1 (es) | 2005-12-14 |
| MXPA06000793A (es) | 2006-04-07 |
| ES2274473T3 (es) | 2007-05-16 |
| ZA200600607B (en) | 2007-05-30 |
| KR100694962B1 (ko) | 2007-03-14 |
| TW200510388A (en) | 2005-03-16 |
| CA2532111A1 (en) | 2005-01-27 |
| RU2006101689A (ru) | 2006-06-27 |
| AU2004256994A1 (en) | 2005-01-27 |
| KR20060030118A (ko) | 2006-04-07 |
| DK1660485T3 (da) | 2007-03-19 |
| PL1660485T3 (pl) | 2007-04-30 |
| JP2006528172A (ja) | 2006-12-14 |
| WO2005007649A1 (en) | 2005-01-27 |
| BRPI0412721A (pt) | 2006-09-26 |
| IL172765A0 (en) | 2006-04-10 |
| EP1660485B1 (en) | 2006-12-27 |
| CN100430388C (zh) | 2008-11-05 |
| NO20056238L (no) | 2006-04-05 |
| EP1660485A1 (en) | 2006-05-31 |
| DE602004003966T2 (de) | 2007-05-24 |
| CN1823060A (zh) | 2006-08-23 |
| DE602004003966D1 (de) | 2007-02-08 |
| PT1660485E (pt) | 2007-01-31 |
| ATE349442T1 (de) | 2007-01-15 |
| CY1105980T1 (el) | 2011-04-06 |
| CO5650232A2 (es) | 2006-06-30 |
| GB0317229D0 (en) | 2003-08-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5833535B2 (ja) | ８−クロロ−１−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンズアゼピンおよびこれに関連する中間体を調製するためのプロセス | |
| WO2006046499A1 (ja) | インドリン化合物およびその製造方法 | |
| CN101568526B (zh) | 阿那曲唑的纯化方法 | |
| RU2593752C1 (ru) | Соединения, пригодные для синтеза бензамидных соединений | |
| TWI291956B (en) | Improved process | |
| US20090099206A1 (en) | Solid forms of (s)-2-amino-3-(4-(2-amino-6-((r)-2,2,2-trifluoro-1-(3'-methoxybiphenyl-4-yl)ethoxy)pyrimidin-4-yl)phenyl)propanoic acid and methods of their use | |
| CN106966947A (zh) | 一种维格列汀的制备方法 | |
| CN111630049B (zh) | 用于制备2-(5-甲氧基异色满-1-基)-4,5-二氢-1h-咪唑及其硫酸氢盐的方法 | |
| JP2004525182A (ja) | 高純度イオヘキソールの製造方法 | |
| JP2004530638A (ja) | 結晶性ベンラファクシン塩基、及び新規なベンラファクシン塩酸塩多型形状、ならびにその調製方法 | |
| WO2012026897A1 (en) | A process for the preparation of imatinib base | |
| JPH0686435B2 (ja) | ベンズアゼピン誘導体 | |
| WO2006018955A1 (ja) | イソインドール誘導体の製造方法 | |
| CN102414198A (zh) | 3-{[(2r)-1-甲基吡咯烷-2-基]甲基}-5-[2-(苯基磺酰基)乙基]-1h-吲哚的合成 | |
| US6927296B2 (en) | Process | |
| KR20070054749A (ko) | 순수한 온단세트론 하이드로클로라이드 이수화물의 개선된제조 방법 | |
| HU230144B1 (hu) | Eljárás quetiapin előállítására | |
| WO2019167058A1 (en) | An improved process for the preparation of propiomazine maleate | |
| JP2013500983A (ja) | フィパメゾールの調製 | |
| JP2016064988A (ja) | １‐（３‐ベンゾイルオキシプロピル）‐７‐シアノ‐５‐［（２ｒ）‐２‐（｛２‐［２‐（２，２，２‐トリフルオロエトキシ）フェノキシ］エチル｝アミノ）プロピル］インドリンの酒石酸塩を製造する方法 | |
| HK1090055A (en) | Improved process for preparing alpha-polymorphic eletriptan hydrobromide |